Ten of America's worst villains, scoundrels and rogues

America has produced an amazing list of illustrious figures over the past three centuries, but we’ve had our share of nefarious characters as well. When I began researching my new book, "Villains, Scoundrels, and Rogues: Incredible True Tales of Mischief and Mayhem (Prometheus Books, March 4, 2014)," I found myself immersed in lurid accounts of seedy serial killers, murdering mobsters, and other horrific psychopaths—the gory fare that seems to be the favorite of “true crime” writers.

To be honest, though, focusing on that brutal crowd can be emotionally draining. That’s why I broadened my inquiries to include a more interesting mix of ne’er-do-wells—everyone from spies, con men, and gamblers to fake mediums, counterfeiters, and medical charlatans.

But people still ask me which of my thirty subjects were the “worst of the worst.” Well, here goes. If these ten characters don’t rank as some of the nastiest people in American history, I don’t know who would. I’ve listed them in chronological order, rather than according to their relative “badness.” I’ll leave that judgment up to readers.

1. William Stoughton—Salem’s Rabid Witch-Hunter

Massachusetts Lieutenant Governor William Stoughton—the homicidal judge who presided over the Salem witch trials of 1692—had no legal training whatsoever. Rigid and prideful, the sixty-year-old bachelor was educated for the ministry but found his calling in colonial politics.


When hysteria broke out in Salem after a group of young girls were thought to have been bewitched, Stoughton was assigned to ferret out the offenders.

In the wildly unjust trials that followed, he demonstrated the ham-fisted tactics of a grand inquisitor, denying defendants representation, allowing witnesses to introduce gossip and conjecture as evidence, and arbitrarily sending nineteen innocent victims to the gallows, fourteen of them women.

Stoughton was later said to have perpetrated “a series of judicial murders that have no parallel in our history.”

2. James DeWolf—Merchant of Misery

James DeWolf was the leading figure in the most active slave-importing family in American history, an elite Rhode Island clan that enjoyed lives of extreme luxury paid for by the suffering of others.

From the early 1700s to the early 1800s, dealing in human chattel earned immense fortunes for many prominent Northern families like the DeWolfs, a heritage that’s unfamiliar to most Americans, who generally associate slavery strictly with the South.

For nearly a century, tiny Rhode Island was responsible for 60 to 90 percent of America’s slaving voyages, led by the towns of Newport and Bristol.

The trade made James DeWolf one of the country’s richest men. DeWolf demonstrated the blackness of his soul in 1790 when he tossed a sick female slave overboard, resulting in an indictment for murder, although the charge was eventually dropped.

3. Samuel Mason—The Cutthroat Captain of Cave-In-Rock

Between the early 1790s and 1803, pirate and highwayman Samuel Mason conducted a reign of terror along the Ohio and Mississippi Rivers and Natchez Trace, making life on the frontier even more perilous.

From a riverside cave in present-day Illinois, Mason preyed on pioneers traveling down the Ohio. After luring passing vessels ashore, Mason and his gang robbed and murdered the travelers—crimes depicted in the movie "How the West Was Won."

Along the Natchez Trace, Mason commemorated his depredations by writing his name in his victims’ blood on a nearby tree.

When Mason was caught in 1803, he had 20 human scalps in his possession. He later escaped but was murdered by two of his own men for the reward that had been placed on their leader’s head—a fitting end for a bloodthirsty predator.

4. John Chivington—Architect of a Tragedy

On November 29, 1864, Col. John Chivington unleashed one of the worst Indian massacres in American history, the slaughter of some 150 Cheyenne and Arapaho women, children, and elderly at Sand Creek, Colorado.

Even though the Indians encamped at Sand Creek had surrendered earlier to a U.S. Army representative, Chivington told his men to take no prisoners, and he stood by as unspeakable atrocities were committed.

Undisciplined and a relentless self-promoter, Chivington hoped that public acclaim over his “victory” would sweep him into public office, although he was disappointed in that regard.

Initially declared a hero, Chivington was later censured by a military investigation and died in disgrace. What made the massacre even more shocking was the fact that Chivington was an ordained minister.

5. Belle Gunness—The Killer They Called "Hell’s Belle"

At the turn of the twentieth century, Norwegian immigrant Belle Gunness became one of the country’s most notorious lonely hearts killers and our worst female serial killer ever.

She’s believed to have slain over 40 people in Chicago and La Porte, Indiana, including her two husbands and all seven of her children, profiting from insurance claims and other scams.

Many of her victims were cash-bearing suitors she lured to her farmhouse with promises of marriage, only to drug and murder them.

In 1908, she faked her own death by killing her maid and her last three children then burning down her house with their bodies inside.

Investigators determined that the adult body was too small to have been that of Gunness, who’d withdrawn her money from local banks days before. No one knows what ever became of this demented creature.

6. & 7. Isaac Harris and Max Blanck—Partners in Perfidy

On March 25, 1911, the greed of New York sweatshop owners Isaac Harris and Max Blanck resulted in the deaths of 146 workers in the tragic Triangle Shirtwaist Factory fire. Harris and Blanck had failed to conduct fire drills or provide adequate safety equipment, and they were so afraid that their seamstresses might pilfer a few scraps of cloth that they locked the door to one of the two stairways leading from their ninth-floor workshop.

When an inferno blocked the other stairway, most of their workers either perished in the fire or leapt from the windows to die on the sidewalks below.

Although indicted for manslaughter, the two owners escaped punishment. They even made a $60,000 profit from the fire, thanks to over-insuring their factory. After families of the victims filed civil suits, Harris and Blanck paid out a paltry $75 for each life lost.

8. Charles Davenport—Keeper of the Immaculate Sperm

In the early twentieth century, biologist Charles Davenport sought to create an American master race of Nordic and Anglo-Saxon Protestants through the pseudoscience of eugenics, or selective breeding. Davenport and his followers advocated immigration restrictions for “undesirable” ethnic groups, the prevention of “unfit” marriages, and sterilization of “defective” individuals.

By the time eugenics lost favor in the 1940s, between 40,000 and 70,000 Americans had been sterilized against their will, mostly minorities or the poor and uneducated.

Davenport’s gravest offense was his support of Nazi scientists in their heinous program of “racial hygiene.”

Hitler himself followed the American eugenics movement, and German leaders even cited this country’s eugenic sterilization laws in their defense at the Nuremberg war crimes tribunals.

9. John Brinkley—The Consummate Medical Huckster

From 1917 through the 1930s, physician John Brinkley made millions of dollars by implanting goat testicles in men to restore their virility.

Fifty new patients a week traveled to Brinkley’s Milford, Kansas, clinic sixty-five miles west of Topeka, eager to pay $750 for an operation that seems laughably suspect today but which, in the early years of the twentieth century, struck many people as perfectly plausible.

The placebo effect often convinced Brinkley’s patients that their potency had been restored. Unfortunately, at least forty-two men died from infections following their operations.

The goat gland doctor’s prosperity ended after he sued the editor of the Journal of the American Medical Association for libel. In the ensuing trial, Brinkley was exposed as a quack, resulting in the collapse of his practice and bankruptcy.

10. Mildred Gillars—The Silken Voice of Treachery

From 1942 to 1945, the voice of frustrated actress Mildred Gillars was beamed around the world from war-torn Europe. Dubbed “Axis Sally” by the Allies, Gillars would become one of the most reviled Americans of her time for her anti-Semitic rants as a German propagandist.

Her efforts to persuade U.S. soldiers to give up their fight against Adolf Hitler would lead to her trial and conviction for treason after the war.

Gillars claimed that she’d done it all because of her love for her boss, saying he’d forced her into becoming a Nazi mouthpiece. The more likely reason was her elevation from abject failure in her own country to artistic success in Germany, where she became the highest paid Nazi broadcaster.

In the end, though, Gillars had bargained away her honor for a pittance and paid for her moment of acclaim with lasting infamy.